1-Naphthaleneboronic acid

Base Information

• Chemical Name: 1-Naphthaleneboronic acid
• CAS No.: 13922-41-3
• Molecular Formula: C10H9BO2
• Molecular Weight: 171.991
• Hs Code.: 29319090
• NSC Number: 78936
• DSSTox Substance ID: DTXSID80930396
• Nikkaji Number: J418.614A
• Wikidata: Q72493436
• ChEMBL ID: CHEMBL415532
• Mol file: 13922-41-3.mol

Synonyms:13922-41-3;1-Naphthaleneboronic acid;1-Naphthylboronic acid;Naphthalene-1-boronic acid;naphthalen-1-ylboronic acid;Boronic acid, naphthalenyl-;(naphthalen-1-yl)boronic acid;1-Naphthaleneboronicacid;1-naphthalene boronic acid;Naphthalenyl-1-boronic acid;MFCD00019722;Naphthylboronic acid;1-naphthalene boronicacid;alpha-NAPHTHYLBORIC ACID;B-1-Naphthalenyl-boronic Acid;CHEMBL415532;1-naphthyl boronic acid;naphtylboronic acid;napthyl boronic acid;naphthyl boronic acid;1-naphtylboronic acid;1-napthylboronic acid;naphthalene-1-boronic;naphthaleneboronic acid;1-napthyl boronic acid;naphthalene boronic acid;1-naphtaleneboronic acid;1-napthaleneboronic acid;1-naphthyleneboronic acid;1-naphthlene boronic acid;1-naphthalenylboronic acid;1-naphthalene-boronic acid;SCHEMBL24488;naphthalen-1-yl boronic acid;1-NAPHTHYLBENZOIC ACID;naphthalene-1-yl-boronic acid;Boronic acid, B-1-naphthalenyl-;DTXSID80930396;BCP22774;NSC78936;BDBM50067896;NSC-78936;AKOS000277862;AC-5373;AS-2649;BCP9000055;CS-W008836;OL10082;PB40513;Naphthalene-1-boronic acid, >=95.0%;NCGC00249474-01;NCGC00249474-02;BP-10052;A3003;AM20060346;BB 0218080;FT-0601799;N0630;EN300-119262;Q-102221;Z336079466;1-Naphthaleneboronic Acid (contains varying amounts of Anhydride);1-Naphthaleneboronic Acid, (contains varying amounts of Anhydride)

Chemical Property of 1-Naphthaleneboronic acid

Chemical Property:

• Appearance/Colour: Off-white to pink beige powder
• Vapor Pressure: 1.63E-06mmHg at 25°C
• Melting Point: 208-214 °C(lit.)
• Refractive Index: 1.638
• Boiling Point: 381.9 °C at 760 mmHg
• PKA: 8.53±0.30(Predicted)
• Flash Point: 184.8 °C
• PSA: 40.46000
• Density: 1.21 g/cm³
• LogP: 0.51960
• Storage Temp.: 0-6°C
• Water Solubility.: 2.5 g/100 mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 172.0695597
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

99%, ^*data from raw suppliers

1-Naphthaleneboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC=CC2=CC=CC=C12)(O)O
• Uses: 1-Naphthaleneboronic acid is a useful synthetic intermediate. It is a reagent used to synthesize potassium aryltrifluoroborates which is a convenient precursor of arylboron difluoride lewis acids. It is also useful in the synthesis of polyaromatic hydrocarbons utilizing the Suzuki reaction. Naphthalene-1-boronic acid can be used:Methyl 5-bromo-2-(naphthalene-1-yl)benzoate, which is a starting material for the preparation of 9-anthracene-spirobenzofluorene host materials.A bifunctional polymer used for the hydrolysis of cellulose.9-(Naphthalene-1-yl)anthracene, which is a key intermediate for the preparation of anthracene derived molecular glass having blue emission.1-Naphthaleneboronic acid can also be as a substrate in fluorometric boronic acid based saccharide sensors based on the Suzuki homocoupling reactions.

Technology Process of 1-Naphthaleneboronic acid

There total 42 articles about 1-Naphthaleneboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

1-Bromonaphthalene (90-11-9) → 1-Naphthylboronic acid (13922-41-3)

Guidance literature:

1-Bromonaphthalene; With tert.-butyl lithium; In tetrahydrofuran; at 78 ℃; for 0.75h;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 4h;

With hydrogenchloride; water; In tetrahydrofuran; ethyl acetate; at 20 ℃;

DOI:10.1002/jhet.27

Reference yield: 84.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-Bromonaphthalene (90-11-9) → 1-Naphthylboronic acid (13922-41-3)

Guidance literature:

1-Bromonaphthalene; With n-butyllithium; In tetrahydrofuran; at -78 - 0 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; for 0.5h; Inert atmosphere;

Reference yield: 83.0%

Triisopropyl borate (5419-55-6) + 1-Bromonaphthalene (90-11-9) → 1-Naphthylboronic acid (13922-41-3)

Guidance literature:

Triisopropyl borate; 1-Bromonaphthalene; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -30 - 20 ℃; for 6h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; hexane; water; toluene; at 20 ℃; for 1h;

upstream raw materials:

(1-naphthyl)dichloroborane

triisobutyl borate

1-naphthylmagnesiumbromide

Trimethyl borate

Downstream raw materials:

2-naphthalen-1-yl-4-(4-nitro-phenyl)-2,3-dihydro-[1,3,5,2]oxadiazaborole

1-(2,6-dimethoxyphenyl)naphthalene

1-phenylnaphthalene

1,1'-bisnaphthalene

Refernces

• 1、 Rondestvedt et al.. "-". . p. 9,11. Retrieved 1955.
• 2、 Bailey, Christopher L.,Murphy, Chris L.,Clary, Jacob W.,Eagon, Scott,Gould, Naomi,Singaram, Bakthan. "Reaction of grignard reagents with diisopropylaminoborane. Synthesis of alkyl, aryl, heteroaryl and allyl boronic acids from organo(diisopropyl)- aminoborane by a simple hydrolysis". . p. 331 - 341. Retrieved 2012.
• 3、 Faraoni,Koll,Mandolesi,Zú?iga,Podestá. "Transmetallations between aryltrialkyltins and borane: Synthesis of arylboronic acids and organotin hydrides". . p. 236 - 238. Retrieved 2000.
• 4、 Mayr, Stefanie,Marin-Luna, Marta,Zipse, Hendrik. "Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols". . p. 3456 - 3489. Retrieved 2021/03/01.
• 5、 Fujii, Ikuya,Semba, Kazuhiko,Li, Qiao-Zhi,Sakaki, Shigeyoshi,Nakao, Yoshiaki. "Magnesiation of Aryl Fluorides Catalyzed by a Rhodium-Aluminum Complex". supporting information. p. 11647 - 11652. Retrieved 2020/08/06.